Our ultimate weekend guide contains 156 unique recommendations of things to do in Pittsburgh in order to help you explore the city every Friday, Saturday, and Sunday of the year (one for each day). With each recommendation, we've also hand selected nearby restaurants, bars, cafes, and shops you may wish to visit while you're in the neighborhood if you have more time!

As always, please keep in mind that our weekend recommendations may vary based on season and typical event schedules. Exact dates and operating hours should be confirmed prior to any visit.

For more information on all recommendations, click through to our full articles or the businesses' websites for more information!

Hundred Acres Manor

One of our favorite things about October is that it means Halloween is just around the corner, and to us there is no place better to go than Hundred Acres Manor in South Park.

This estate is one of the largest destinations for haunted attractions in the city, and is consistently rated among the best in the nation. Feeling brave?

Wooden Door Winery

Wooden Door Winery near New Kensington is located on a quaint homestead that just begs you stay a while to drink wine and watch the day go by.

In the fall this winery starts rolling out their fall and winter wines, so be on the lookout for their Autumn Riesling- one of our very favorites. Or, if you're looking for something a bit different, no one will judge you if you try a wine slushie, they're amazing!

If you make it out to this winery on a beautiful day, make the small detour to Harrison Hills Park for a hike!

Moraine State Park

It is a bit of a drive to get to Moraine State Park, but those who make the effort to journey about 45 minutes north of the city to visit this one will be rewarded with gorgeous lake views, hiking trails that pass through numerous natural viewing areas, and all-in-all, a great day of exploring.

Before coming home, be sure to stop at the The Snowman- an iconic ice cream shop that serves up shaved ice and soft serve ice cream that is the perfect reward after a long day of hiking.

Opera in the Cultural District

As fall comes back to the Burgh, you may want to start going back inside. Luckily, there are many shows to check out in the Cultural District throughout the year including those by the Pittsburgh Opera!

Kennywood Phantom Fright Night

Kennywood makes a rare second appearance on this list during October for their Phantom Fright Nights haunted houses. During the weekends of October the park is transformed into a theme park of horrors full of haunted houses and thrilling rides.

If you have some more time in the afternoon before Kennywood Fright Night, schedule a tour of Trundle Manor to get you in the horror spirit!

North Shore River Trail

When it comes to viewing the fall colors, you have many options both in and out of the city. One of our favorite spots in the city limits is the North Shore River Trail which spans several miles west and east of the city.

Pick up your bike at one of the many Healthy Ride kiosks in downtown or the North Side and check out the sights like the Mr. Rogers memorial, PNC Park, and of course, the stunning views of the city.

There are a number of awesome attractions and restaurants along the North Shore River Trail By the Science Center is the USS Requin Submarine, and for those making a bigger walk or ride can cross the river and head down to Gaucho or Lidia's in the Strip District!

Arsenal Cider House

Although you can enjoy Arsenal Cider House any time of the year, we think this one is worth visiting in the fall at the height of apple season.

As a special bonus, Arsenal Cider House rolls out their fall and winter flavors around this time, which are some of our favorites of the bunch. Be on the lookout for events here, as Arsenal's outdoor space is the perfect spot to let the night roll by with live music or a food truck!

McConnells Mill State Park

Located about 45 minutes north of the city, McConnells Mill State Park is perhaps our favorite state park in Western Pennsylvania. This one has a historical mill, a covered bridge, and miles of hiking trails for those looking for a long day out.

Pittsburgh Ghost Tour

Looking to get acquainted with Pittsburgh's dark side? A pre-Halloween ghost tour is in order with the folks at Haunted Pittsburgh.

This two-hour tour covers some of the city's most famous hauntings- hilarious, insidious, and otherwise.

Workshop PGH

With the slogan of “Drink Beer, Make Stuff,” you already know what you're getting yourself into at a Workshop PGH event.

This artist space in Garfield is one of many that have opened up recently in the neighborhood, and offers weekly workshops to learn skills such as screen printing, candle making, or wood working!

Want to grab a bite to eat before or after your class? Check out Umami or The Vandal in Lawrenceville, or Paris 66 in East Liberty.

Steelers Game

Here we go! By mid-October football season is in full swing, which means its time to head down to Heinz Field to cheer on the Pittsburgh Steelers as they make their bid for yet another Super Bowl ring. Just don't forget your Terrible Towel!

Share on Social Media and Read Next Month’s Recommendations!

Did you find this month’s recommendation helpful? Use the buttons at the bottom of this page to share on social media!

For more recommendations, click the month or season based on your preference using the links below. Otherwise, click the links below for next month’s recommendations!